PERAZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H25N3S
Molecular Weight	339.498
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCN(CCCN2C3=C(SC4=C2C=CC=C4)C=CC=C3)CC1

InChI

InChIKey=WEYVCQFUGFRXOM-UHFFFAOYSA-N

InChI=1S/C20H25N3S/c1-21-13-15-22(16-14-21)11-6-12-23-17-7-2-4-9-19(17)24-20-10-5-3-8-18(20)23/h2-5,7-10H,6,11-16H2,1H3

HIDE SMILES / InChI

Molecular Formula	C20H25N3S
Molecular Weight	339.498
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/16625562
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/12523495 and http://www.genome.jp/dbget-bin/www_bget?D01412

Perazine (Taxilan) is a moderate-potency typical antipsychotic of the phenothiazine class. Perazine is an older antipsychotic drug first introduced in the 1950s. It is suggested to have a low level of side effects (especially for movement disorders). Its use is regional and restricted to countries like Germany, Poland, the Netherlands and the former Yugoslavia. Perazine has being shown to be a potent inhibitor of human CYP1A2. It acts as a dopamine antagonist.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: http://www.ncbi.nlm.nih.gov/pubmed/12523495	Inhibitor 8297
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: http://www.genome.jp/dbget-bin/www_bget?D01412	Antagonist 2778
Cytochrome P450 2B, Rattus norvegicus 2 Target ID: Cytochrome P450 2B, Rattus norvegicus Sources: http://www.ncbi.nlm.nih.gov/pubmed/18048963	Inhibitor 8297	45.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11869638	Primary		Approved 8429	Taxilan Approved Use Taxilan is used in the treatment of schizophrenia

PubMed

Title	Date	PubMed
Neurologic complications in patients treated with lithium.	1988 Sep	3054982
[Electroconvulsive therapy in treatment of acute life threatening catatonia in toxic epidermal necrolysis (Lyell syndrome)].	1992 May	1603193
An acute psychotic disorder caused by pefloxacin: a case report.	1996 Feb	8861197
Schizophrenia.	2003 Dec	15555143
Which neuroleptic would psychiatrists take for themselves or their relatives?	2003 Feb	12648897
Effects of cytochrome P-450 inducers on the perazine metabolism in a primary culture of human hepatocytes.	2003 Jul-Aug	14581727
Screening, library-assisted identification and validated quantification of fifteen neuroleptics and three of their metabolites in plasma by liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization.	2003 Mar	12644990
Antipsychotic efficacy of the antidepressant trimipramine: a randomized, double-blind comparison with the phenothiazine perazine.	2003 Mar-Apr	12734763
Identification of P-glycoprotein substrates and inhibitors among psychoactive compounds--implications for pharmacokinetics of selected substrates.	2004 Aug	15285840
Blood dyscrasias induced by psychotropic drugs.	2004 Mar	15052517
Inhibition of rat liver CYP2D in vitro and after 1-day and long-term exposure to neuroleptics in vivo-possible involvement of different mechanisms.	2005 Jan	15572279
Direct effects of neuroleptics on the activity of CYP2A in the liver of rats.	2005 Nov-Dec	16382210
Effect of chronic treatment with perazine on lipopolysaccharide-induced interleukin-1 beta levels in the rat brain.	2006 Apr	16583240
Automated analysis of quetiapine and other antipsychotic drugs in human blood by high performance-liquid chromatography with column-switching and spectrophotometric detection.	2006 Jan 18	16337441
Characterization of human cytochrome p450 enzymes involved in the metabolism of the piperidine-type phenothiazine neuroleptic thioridazine.	2006 Mar	16272405
Typical and atypical antipsychotics--the misleading dichotomy. Results from the Working Group 'Drugs in Psychiatry' (AGATE).	2008	18515977
Increased D-amino acid oxidase expression in the bilateral hippocampal CA4 of schizophrenic patients: a post-mortem study.	2009 Dec	19823762
Effects of typical and atypical antipsychotic drugs on gene expression profiles in the liver of schizophrenia subjects.	2009 Sep 16	19758435
[Perazine in the treatment of psychotic disorders--research review].	2010 May-Jun	20672521
Main contribution of the cytochrome P450 isoenzyme 1A2 (CYP1A2) to N-demethylation and 5-sulfoxidation of the phenothiazine neuroleptic chlorpromazine in human liver--A comparison with other phenothiazines.	2010 Oct 15	20615392

Patents

Sample Use Guides

In Vivo Use Guide

The customary dose range recommended for this antipsychotic under in-patient conditions is 75-600 mg/day (maximum 1000 mg/day).

Route of Administration: Oral

In Vitro Use Guide

About 80% of basal human CYP1A2 activity was reduced by the therapeutic concentrations of perazine (5-10 uM).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:18:23 GMT 2023` Edited by `admin` on `Fri Dec 15 16:18:23 GMT 2023`
Record UNII	8915147A2B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PERAZINE

Common Name

English

PROCHLORPERAZINE MALEATE IMPURITY B [EP IMPURITY]

Common Name

English

10-(3-(4-METHYLPIPERAZIN-1-YL)PROPYL)PHENOTHIAZINE

Systematic Name

English

PERAZINE [MI]

Common Name

English

Perazine [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN05AB10